


An Unconventional Convention

by Dangerousnotbroken, Petrichor_Amber



Series: An Unconventional Convention [1]
Category: Doctor Who (2005), Supernatural, Torchwood
Genre: Anal Play, Anal Sex, Bottom Castiel, Bottom Dean, Bottoming from the Top, Drunk Sex, Explicit Language, Explicit Sexual Content, First Time, First Time Blow Jobs, Hand Jobs, M/M, Multi, Multiple Orgasms, Oral Sex, Threesome - M/M/M, Top Castiel, Top Jack
Language: English
Status: Completed
Published: 2014-11-03
Updated: 2014-11-03
Packaged: 2018-02-23 22:11:18
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 11,142
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2557553
Author URL: https://archiveofourown.org/users/Dangerousnotbroken/pseuds/Dangerousnotbroken, https://archiveofourown.org/users/Petrichor_Amber/pseuds/Petrichor_Amber
Summary: <blockquote class="userstuff">
              <p>Dean attends these stupid conventions for Chuck's sake, partly to appease him, partly to ensure the man never prints another goddamn Supernatural book. Except for when he's at the front of the room, no one can tell him apart from the scores of jerks dressed like him, and he takes solace in the anonymity and the bottle. Tonight though, tonight is different, and he has no idea what fate has in store for him. Or for Castiel.</p>
            </blockquote>





	An Unconventional Convention

**Author's Note:**

> Once upon a time, Petrichor_Amber and DangerousNotBroken had a super random and totally inappropriate conversation about how hot a threesome between Jack Harkness, Dean Winchester, and Castiel would be. And since neither of them could decide who was better suited to write it, they decided to write it together. _Because that’s what people do._ The following work of fiction is the result of that insanity. 
> 
> Enjoy, ladies and gents, and leave your impressions in the comments. If it’s well received, who knows, these two crazy cats might write some more collaborative smut!

He hated these. He hated when Chuck roped him into making a “special appearance,” he hated when he had to deal with dicks pretending to be him and his brother, and most of all he hated how he actually liked when it turned out poorly, ‘cause at least then it gave him something to do. It had been a long day, and he was grateful to be done, sitting down at the bar, and ordering a beer.

“Hey there, Dean.”

“Man I am so not in the mood, so why don’t you just –” His protest was cut off as he looked up and saw the most flirtatious grin he had ever seen (outside of a mirror) staring back at him. It was simply unfair how distracting Dean found that smile, especially considering that the guy wasn’t his type at all. Mostly, because, well, he was a guy.

“Sorry ‘bout that. Just thought after the day you’ve had you could use a drink and some company.” He said it with a casual arrogance that did nothing to lessen his very clear come on, and Dean found himself getting more and more frustrated.

“As a matter of fact, I could, but that doesn’t mean I want it from you, and what the hell is that supposed to mean, anyway, ‘after the day you’ve had’?”

The stranger shrugged, dropping his piercing eyes back to his whiskey and taking a sip before answering him. “It must get frustrating dealing with all these hunter wannabes.”

“Excuse me?” There’s no way this guy could know, no way he would be able to tell him apart from anyone else there wearing a henley and a leather jacket. He glared at this tall stranger, sitting at the bar in a blue dress shirt caged by suspenders, like it was 1943 or something.

“Just, you’re clearly Dean Winchester, so I imagine this is all a bit of a bore for you.”

“Ya, good job there detective. You work that out all on your own?” Dean shook his head with a chuckle at how weak this guy’s game was, and took a swig of beer while looking across the bar to see if there were any chicks worth approaching tonight, anyone he could pull the whole “big damn hero” thing with.

“I believe you misunderstood me.” The stranger laughed quietly, smiled, and then made purposeful, intense eye contact with Dean. “I didn’t mean that you’re clearly pretending to be Dean Winchester. I mean that you are clearly _actually_ Dean Winchester.” He held Dean’s gaze a second longer, daring him to not engage in this exchange, and then returned to his whiskey.

Dean didn’t know what to do. He was angry; angry as hell, but he didn’t want to let him know he’d got to him, so he decided to try and play it cool. Try to pretend that this wasn’t messing with his head as he looked at the man’s strong hands, his full lips.

“Oh ya? And what exactly gave you that impression?”

The man smiled at him again, but this smile was different. The flirtation was gone, it was just a sad smile, a smile that had endured far too much. That hid too much.

“Everyone _pretending_ to be Dean is strutting around the place like they just got a promotion, like they’re not used to this amount of authority. Their eyes smile behind their scowls because they think that to be Dean Winchester means to glower seductively, to take epic road trips with classic tunes, and to save the world and be the hero. But you…” He paused to take a sip of his whiskey, swilled it around in his mouth as if hunting for the right words. “You, Dean,” he emphasized his name in a way that Dean couldn’t quite handle, “you walk in and you actually own the place, and your smile tries to hide eyes that have seen too much. Eyes that know that it’s lonely, and dangerous, and that you lose the people you love along the way.”

Dean wanted to protest, wanted to tell this stranger to go fuck himself, but he was too accurate. Struck too close to home. And Dean could see that the guy knew what he was talking about. That pause he had felt, the shift. That could only be explained by the fact that this guy had been out there. Maybe not as a hunter, but he knew. Dean decided not to punch him, and actually thought about asking him to be his new best friend, which was saying something, because Dean hated the idea of asking anybody for anything. But there was no way in hell he was going to show his cards.

“And just how exactly did you see all this mumbo jumbo, you got magic eyes?”

The stranger looked away, and suddenly seemed much older, much more vulnerable. “It takes one to know one.” And he knocked back the rest of his drink. So he was right. Guy had been around.

“Captain Jack Harkness,” he added, as if that explained everything.

“Well, thanks for that,” Dean grumbled and took another pull at his beer. It was empty now, which did nothing to improve his mood. The entire concept of these conventions got on his last nerve. He was just grateful that Chuck had kept up his promise not to publish anything new. Sam had threatened him, but still. It was bad enough that these people thought they knew his life from what had made it in to the books. It’d be worse if they knew about what happened after he went to Hell. Dean lifted his head and his eyes searched for the bartender. When he found the balding man in the apron, he gestured with his empty bottle.

The bartender just nodded disinterestedly and pulled another beer out of the cooler, prying the top off before setting it down in front of Dean and discarding the empty. Dean was about to reiterate how much he was not in the mood for this shit when he caught sight of a familiar mop of hair enter the bar. Even at a distance, it was obviously the real Sam and not a douche in a Sam costume. The height was a dead giveaway, and the hair was clearly not a wig like the ones worn by most of the assholes who dressed up as his brother at these things. Dean heaved a sigh of relief and waved at his brother. Anything to rescue him from conversation with this hormonal fanboy.

When Sam approached, he wasn’t alone. Dean found himself happier than he had a right to be when the younger Winchester strode up to the bar with Castiel at his side.

“Hey Dean. I’m surprised to see you’re not day-drinking alone,” Sam teased with a laugh. He perched on the barstool next to Jack and leaned his elbows on the bar. Dean shot him a dirty look that Sam ignored entirely.

“Captain Jack Harkness,” sang Jack in that smooth voice, reaching out towards Sam for a handshake. Dean rolled his eyes. “You must be Sam.”

“Jack,” Dean explained with considerable venom in his voice, “has decided I’m not just…what’s the word Sammy? Cosplaying? Is that what you call it? Anyway, Jack says he can tell I’m not pretending to be Dean. Apparently it’s really, really obvious that I’m the real thing. Jack knows me _so_ well.” He shook his head and turned his attention back to his beer. Dean just wished Jack would go away.

“What can I say, the books do an impeccable job of describing your personality. Although I have to say you’re taller in real life. And you have more freckles.” Jack ignored the flush on Dean’s face at these words and turned his attention to the newcomers. “Can I offer you boys a drink?”

“No thanks man. I have to go do a panel interview with Chuck in like five minutes. He bribed me with technology,” Sam replied, gesturing to the fancy new tablet tucked into his shoulder bag. “You guys drink one for me.” As Sam stood to walk away Castiel stepped around him and sat on the seat he’d just vacated. In his desperate hope that Jack would take off Dean had nearly forgotten he was there.

“So what do you think of your first convention, Cas?” Dean forced a smile at the blue-eyed angel’s look of consternation.

“I find the entire concept perplexing,” he mused with that trademark squint narrowing his eyes.

“You and me both, buddy.” Dean agreed.

“And who is this stunning creature?” Jack interjected, grinning wolfishly at Castiel. He made no effort to hide the once-over he gave the trench-coat clad man.

“I am Castiel,” he replied flatly, leveling Jack with an unreadable look.

“Just one name? Like Cher?”

“I don’t understand that reference.” Castiel stated, then fell quiet.

“So Dean,” Jack began, placing a hand on Dean’s forearm in an incredibly familiar gesture. “If you hate these conventions so much, why are you here?” Dean eyed the hand like he would a viper. He wanted it gone, but he felt paralyzed to do anything about it.

“I’ve asked myself the very same question. I guess I feel like I owe Ch…uh, Carver Edlund. We’ve been through some shit.” He shrugged.

“If half of what he’s written is true, I’m not sure you owe anyone anything. I think the world owes you.” Dean shrank under the weight of Jack’s eyes. He didn’t look up but he could feel them boring in to him. He suddenly felt very small.

“I’ve told him the same on many occasions,” Castiel chimed in. “He has a tendency to be quite reductive about his own worth.”

“Cut it out guys. I feel like I’m getting it from all sides here.” Dean focused all his attention on his drink.

“That could be arranged,” Jack said smoothly, and Dean choked on the last drops of beer in his bottle. “There’s a booth just opened up over there. Come on. You two should have a drink on me.” He stood up and grabbed the heavy overcoat resting on the back of his bar stool.

“Thank you,” Cas answered, trying to be polite and happy to practice his “people skills” that the boys always criticized. Dean couldn’t think of a worse time for Cas to finally start being nice to strangers.

“Cas, no!” Dean whispered urgently, trying to catch his eye and stop him from agreeing to this ludicrous sham. But it was too late, and unfortunately Jack heard him.

“Sorry gorgeous, you’re outnumbered.” That grin again, just playing with Dean, toying with him like a cat before pouncing on a mouse. Except Dean didn’t like being the prey, and he certainly didn’t like being pounced on by strange know-it all dudes at the bar.

But Cas was already following Jack to the booth, and there was no way on earth, or hell, or heaven, for that matter, that Dean would abandon Cas to this lunatic, so he sighed, and trudged after them. He made sure to catch the bartender’s eye before taking off, making sure that if he had to endure this, at least he could take the edge off.

When they arrived at the booth Jack nimbly slid into the back, in the centre. When Dean raised an eyebrow Jack shrugged, and simply answered “I figured you wouldn’t appreciate being pinned down. At least not yet. Plus this way I get to sit between two gorgeous gentleman, so honestly, I think I’m getting the better deal here.”

Dean snorted derisively, trying to ignore how thoughtful that was, how perceptive Jack seemed to be, despite his posturing. The flirting helped him not take it to heart too much. He sat down to Jack’s left while Cas sat to the man’s right, and Dean stole a glance at Cas, across from him and smiling calmly like this happened all the time. Dean shook his head at how ridiculous Cas was, but he felt his body relax a little at the familiar smile. At the very least this nightmare would make a great story.

“So, Jack,” Dean tried the word, like it might kill him to be civil to this guy. “What exactly do you do? How do you know what it’s like?” Jack’s eyes widened ever so slightly, and his lips started to tug into a grin when Dean realized what he just said. “What it would be like. If, you know, uh, you were right.” Cas stared at him from across the table like he was perhaps honestly the dumbest human to ever exist. Dean responded with a covert “what?” mimed through a shrug and non-committal frown.

There’s no way he missed that exchange, but Jack did them the courtesy of pretending he did anyway. “I’m not just a fan,” he said quietly, so low that Dean barely heard him. Jack clearly perceived the oppressive pause that followed, and tried to make a joke of it. “I’m no hunter, if that’s what you’re thinking. But I’ve…I’ve seen some things.” He smiled but it was empty, and Dean was surprised to see the glint gone from those eyes.

Just then the bartender brought their next round, which bought Jack some time, and by the time he had left he was back to his ridiculously happy and flirtatious self.

“So, angel, what’s your story” Jack turned to Cas, arm propped up on the backrest. Cas looked horrified and Dean actually choked on his beer.

“I don’t understand, how could you possibly know that?” Cas looked to Dean, waiting for guidance on what is considered “polite” when someone perceives that you are in fact a being of celestial intent.

“Damnit Cas.” Dean just sighed, knowing it was too late to do any kind of damage control.

Jack just looked back and forth between the men, like he was watching the slowest game of tennis ever. “No….?” At last he exhaled long and slow, and Dean actually heard him whistle. Seriously, what the hell is this, some old war movie? But then Jack chuckled again, and Dean couldn’t remember ever meeting someone who chuckled that much, and suddenly everything was fine again. He heard Jack whisper, “Well I’ll be godamned.”

Jack looked up at Castiel, flashed him the smile that should be illegal, and simply asked “An angel and a hero. How on earth did I get so lucky?” Dean snorted, knowing full well it was discourteous. His drink was empty again. That would never do.

“Trust me man, you want nothing to do with angels. ‘Cept for Cas here, they’re all winged douchebags.” He waved for the bartender. When he arrived, instead of ordering another beer he asked the guy to just bring a whole bottle of whiskey. Dean couldn’t imagine anything else that would make this encounter bearable.

Jack talked a lot. Like, a lot. Dean tried to tune him out but Castiel seemed content to listen to the guy’s obviously altered stories and sip quietly at his whiskey. It didn’t take long for them to drain the bottle.

“Not often I run in to someone who can match me for whiskey,” Dean noted, impressed. He poured the last of the bottle between the three glasses. “I mean Cas, last time _he_ went on a bender he literally drank a liquor store, but you’re holding up ok. Not bad.”

“Is he always this competitive?” Jack asked, directing the question to Castiel. The angel just shrugged.

“I’m not competitive,” Dean countered. “I’m just awesome.”

“Is that a fact?” Jack replied with a mischievous grin. “So if I were to tell you I think I could probably out-drink you, you wouldn’t take the challenge as an affront to your manhood?”

“I might laugh at you, because there is like, _no way_ that’s true. But my manhood would be in no way involved.”

“That’s a shame,” Jack murmured into his glass.

“Excuse me?” Dean replied, scarcely believing the guy could actually be that bold.

“I said I bet you’re just afraid you’ll lose.” Dean downed the last drops of his whiskey a little too quickly and glanced at Castiel. His glass was already empty. Dean hadn’t even seen him lift it, but the angel wore a glower he wasn’t used to seeing outside of those situations where someone was about to be smote.

“You,” Dean warned as he stood up from the table, “are totally going to regret that. C’mon Cas. I got a bottle in my room.”

 

“And what happens if I am the victor?” Castiel asked as they stepped off the elevator. Dean’s room was on one of the higher floors of the hotel, with view of the city that he’d been told was fantastic but hadn’t bothered to look at yet. He was just happy it was nicer than the motels they stayed in on hunts, and that he had the room all to himself.

“Nothing happens, Cas. No one doubts that you can handle more liquor than either of us. This is between me and Jackie-boy.” Dean didn’t catch the way Cas’ eyes narrowed at the last comment, but Jack did.

“Don’t worry about it, Castiel. I’m just going to drink your boyfriend under the table,” Jack boasted as they drew to a stop outside Dean’s room, and Dean fished in the pockets of his jacket for his key-card.

“Woah there, back that truck up. Castiel is _not_ my boyfriend!” Dean protested loudly. Once they were all inside he let the door slam shut behind them and tossed his jacket over the back of a chair.

“This is correct, Jack. Dean is my friend. We have endured many difficult situations together, but our relationship is not one of a romantic nature.” The angel stood in the middle of the room awkwardly, as per usual. Jack paced casually around for a moment before responding; it was definitely a bigger room that Dean was used to, and he decided to go sit on the edge of the bed, near where Castiel was hovering.

“Oh man…I thought…I thought you two knew! You mean you really never figured it out?” Jack asked incredulously. “Have you seen how he looks at you?” Neither man was sure which of them was the subject of that sentence. “Have you not noticed how close you stand? You two have it bad!” Jack’s chest shook with laughter as he finished his circuit of the room.

“That’s not…” Dean began. “I mean…come on man…you can’t really believe…” Dean found himself at a loss for words. He told himself it was because what Jack was proposing was too ridiculous to speak of.

“So it won’t bother you at all if I do this, then,” Jack stated cryptically, and before Dean had a chance to demand an explanation Jack had his hands on either side of a very startled Castiel’s face, and their lips were locked in a messy kiss. Dean could not believe his eyes. He hadn’t expected that. And if he had anticipated it, he certainly wouldn’t have expected Castiel to kiss the guy back, not with that much enthusiasm. And even if he’d seen all of that coming, he’d never have guessed how much it would bother him.

Dean found himself striding across the room without really thinking about his actions. He pulled Jack off of Castiel with rough hands and threw him roughly away from the startled angel.

“What the hell, man?” He barked, but Jack just looked at him with that wolfish grin, his lips wet and red from the offending kiss. And then Jack was kissing _him_ , and Dean could taste the whiskey on Jack’s breath. He’d never kissed a man before, but it was surprisingly easy, even with the stubble across Jack’s jaw making it impossible to pretend he was with a woman. Jack was aggressive and demanding, and Dean had no idea how long the kiss carried on before he felt hands on his shoulders and he was tugged away from the enigmatic stranger. His eyes fell on Castiel’s then, eyes that were alight with a fire he was not used to seeing there. And Dean would never be able to decide who started it but someone moved. His lips crashed into Cas’ or maybe it was the other way around, and _holy fuck_ , he was kissing Castiel.

Dean’s mind went blank. He didn’t care about denying it anymore. He’d thought about Cas like that, sure, but he could barely admit it even to himself. He had realized long ago that the two of them did not act like just a pair of friends. Had imagined what it would be like to one day touch his angel’s face, caress those lips. But nothing he had ever imagined, even in his most adventurous subconscious, had prepared him for this moment. Dean felt Cas encircle him, wash over him, and he was overwhelmed by the affection, the tenderness, and the desire in that kiss. It was like Cas had his wings still and had enveloped him, wrapped them up into this perfect moment and they were the only two people in the world.

Suddenly he felt gentle, tentative hands on either side of his waist, and he was shocked back to reality, and to the brutal truth that he and Cas were not alone in the world. They weren’t even alone in this room. But he couldn’t stop kissing Castiel, not now that they finally were. It was like he had been in withdrawal and had no idea this was what he needed, and now that he did, he wanted to drink in as much of Cas as he possibly could, so he ignored Jack. This seemed to suit Jack just fine, as he slid his hands around to Dean’s chest, careful not to intrude on their kiss, and Dean felt deft fingers start to undo the buttons of his shirt. Once Jack’s task was completed, he dragged his hands up to Dean’s shoulders, and slowly slipped the overshirt off, sliding his hands down over Dean’s now mostly exposed arms, tucking a finger under the tshirt sleeve to let Dean know how much he wanted to touch there too, if that was in the cards. The whole time Cas clutched Dean’s neck and kissed him like the world was about to end and it was so much that Dean felt himself hardening, surprised that attention from two guys was doing things to him he never expected.

He realized he was feeling lightheaded as much from the situation as from the fact that he and Cas hadn’t broken their kiss in an awfully long time, and he pulled away to breathe, instantly regretting it and the empty feeling that rushed in along with the air. Cas looked at him inquisitively, eyebrows knit together in consternation, and Dean felt he needed to be clear with Cas. Make sure he understood the consequences if they continued.

“Cas, are you ok?” He asked gently, running his thumb along Castiel’s jaw line, and Cas in turn nuzzled his face into Dean’s palm, sighed with a contented murmur. “Are you sure you want to do this?”

Castiel stared deep into Dean’s eyes with the look that always made him feel like he was seeing his soul, appraising his innermost thoughts. “Dean, I’m…I didn’t realize it was this, but I’ve felt…for a long time now, I just didn’t….” He took a deep breath and nodded. “I’m certain.”

“I know you haven’t really, well, y’know. We’ll take this slow, we’re not going to do anything you don’t want to. You say stop and it’s over, immediately. Ok?” Cas nodded, and Dean nodded back, confirming to Cas that he would take care of him, protect him, and be with him.

“Castiel, you’ve never used your body for pleasure?” Castiel and Dean started a little, having almost forgotten the man’s presence again. Jack questioned him softly, with no hint of judgment or pressure, just confirming that he had understood Dean properly. When Cas shook his head, confirming Jack’s interpretation, Jack smiled, not hungrily like before, but like he had opened up the best Christmas present imaginable. He turned to Dean and said conspiratorially “Then let’s show him how much fun it can be.” And he winked before gently kneeling in front of Cas.

Dean realized what Jack was about to do, and couldn’t handle the thought of him making Cas feel that good without him, didn’t want to hear Cas make a sound he wasn’t responsible for, and he grabbed Cas’ neck again in his fervor, pulling his lips back to his, and kissing Cas with all the want he’d bottled up for so long. He poured his longing into that kiss, hands on either side of Cas’ face, grasping at it greedily as he finally told Cas with actions what he never could have with words. Dean had never really been much for talking anyway.

Dean was standing so close to Castiel that he felt Jack’s hands on Cas’ hips, felt them reach Cas’ belt and hesitate. Dean pulled back to breathe again and saw Jack looking up at Castiel, waiting for confirmation, for his consent. Cas just looked back up at Dean and nodded. Without having said anything, it was clear to all of them that this was Dean and Castiel’s evening, Jack just wanted to further it however he could. Dean took advantage of the temporary distance between them to slowly slide off Cas’ tie. He pushed the jacket off and let it fall behind them, and began to unbutton his crumpled white shirt. For the first time since Cas had raised him from Hell Dean finally saw the angel out of that outfit, and he found it breathtaking. He had no idea Cas’ shoulders would be so well defined, that his hipbones would protrude just so out of the top of his waistband. And before he could take in any more they were drawing each other in again, kissing deeply, passionately, making up for so much lost time.

Dean knew from the hitch in Cas’ kiss when Jack first palmed him. At first Dean felt jealous, wanted to be the one making Cas gasp like that, but he quickly forgot his resistance when Cas moaned into his mouth, sending a reverberation right through Dean and down to his throat, and goddamn if that wasn’t the sexiest thing Dean had ever heard in his entire life. And suddenly he couldn’t stop himself, he was running his hands all over Castiel’s body, exploring the flesh that had been beside him for years but always just out of reach. Cas was clearly distracted, but he managed to grab Dean’s t-shirt and slide it over his head, exposing his chest and the rest of his arms, and then Cas was kissing every inch of Dean’s upper body as if he were starving for it, devouring him.

Dean was distantly aware that the entire encounter should be so, so weird for him. Everything about it went against his better judgment, but he found it surprisingly easy to suppress the panic that rose in his chest as Castiel left a trail of wet kisses across his collarbone. The angel was inexperienced, that much was true, but he was learning exceptionally quickly, and every touch of his hands, his lips, left Dean’s skin on fire. Dean glanced down to where Jack knelt at his right. Somewhere in the few moments they’d been at this Jack had managed to drag Castiel’s pants down over the hipbones Dean had only just learned to appreciate, and was working to liberate Cas’ substantial erection from his plain white boxers.

Dean stifled a gasp as Jack freed Cas of his shorts and his eyes fell on Cas’ cock for the first time. His mind was immediately flooded with images of the things he could do with it; how it would feel to wrap his hands around the thick shaft and the noises Cas would make when he did, what it would be like to take Castiel in his mouth and do all the things he liked to have done to his own cock.

He didn’t realize he’d been staring until he felt Castiel’s hand cup his jaw and tilt his face upwards. Cas’ eyes were dark with lust and his lips were parted just slightly. Dean took another moment to appreciate how delicious he looked, all flushed and desperate, before claiming those lips again. Cas was all his now. Almost.

As if Jack could hear his thoughts, the second Dean mentally acknowledged the presence of the third man in the room he felt a hand on his wrist. Jack’s hand guided Dean’s off of Castiel’s chest and down, and Jack’s fingers wrapped Dean’s around Castiel’s shaft. Their hands moved in tandem for a few tentative strokes before Jack let go. Dean continued the motion, focusing on the little whimpers Cas made against his mouth as he stroked his length. Castiel was so inexperienced, so new to this. Dean forced himself to remember that. He had to make sure Cas knew how good this could feel.

He was so wrapped up in making Cas feel good that he didn’t notice Jack moving until he felt hands on his own belt buckle. Jack stood behind him now and he could feel Jack’s hips pressed against his ass. He could feel Jack’s _dick_ pressed against his ass. As if sensing the apprehension rising in Dean’s core, Jack planted soothing kisses along his shoulders and the back of his neck. Jack’s hands worked expertly at Dean’s belt and fly. He felt himself inhale sharply as his jeans fell to the floor, where they were quickly followed by his boxers. If there was ever a moment to hesitate, to call a stop to this insanity, it would be now.

Dean let the moment pass. Any thoughts he had of calling a halt to the encounter flew out the window when Jack took his cock in hand, stroking it slowly and gently, just as he had with Cas’. Jack was kissing his shoulders, his back, and the rough fabric of Jack’s trousers pressing against his bare ass was a wholly unfamiliar sensation, though it was difficult to deny that he liked it. His hips rocked forward, chasing the friction of Jack’s hand, and he was vaguely aware that he should stop then because there was _a dude’s hand wrapped around his dick_ , but he just could not be bothered.

Instead, he tilted his head and dragged his lips down Castiel’s neck. He left whisper soft kisses on the tender skin of his throat, let his teeth graze against the protrusion of his collarbone, ran his tongue along the dip between his pecs. Cas’ hands came up to rake through his hair as Dean’s mouth closed around the pert nub of Cas’ left nipple, and the sound that fell from Cas’ lips then was positively filthy. Dean wanted to hear more. His teeth joined his lips, biting down just slightly. Cas groaned. Dean’s tongue swirled and flicked, and Cas let out something akin to a whimper. _If that’s what he sounds like from this,_ Dean thought, _I wonder…_

Dean acted before he finished the thought, sinking to kneel in front of Cas. The carpet was soft under his knees, but he was more interested in the hard length of Cas’ cock. He flicked his tongue across the tip experimentally. The angel’s whole body responded. His fingers tightened in Dean’s hair, breath stuttering, and if Dean wasn’t mistaken, his knees threatened to buckle. Jack had circled behind Cas now, and helped steady him as Castiel responded to the unfamiliar sensation. Spurred on by Cas’ favorable response, Dean licked his way down Cas’ length then back up to the tip, before taking as much of Cas in to his mouth as he could fit.

The cry that escaped Cas’ lips was inhuman. Dean thought he might come right now just from hearing it, feeling Cas’ fingers clutching him closer, feeling him buck into his face. Dean had no idea it would feel so natural to do this; part of him had assumed he would freak out if he tried to suck a cock, but it wasn’t like that. He was sucking off Cas, tenderly taking him in and making him moan and gasp and it was the most incredible thing Dean had ever done.

He worked his right hand along Cas’ base, mimicking the movements of his mouth and extending the sensation. He alternated sucking hard with sliding up and down loosely, flicking the length with his tongue, and it was excessively clear Cas liked what he was doing. With his left hand Dean grasped Cas’ hip, thumb gripping the bone and fingers digging into his ass, pulling him closer. He wanted to take in every last bit of Cas.

Suddenly he felt a hand over his, and he found himself fighting with Jack for Cas’ flesh. Dean lost track of who was touching what part of Castiel, it was all hands and mouths, but when he tentatively slid his left hand down to caress Cas’ balls his fingers grazed Jack’s, who was already rubbing back and forth on Cas’ perineum.

Jack was still nearly fully clothed, and for a second Dean felt bad about neglecting him so much. Jack must have read his face, because he cheekily thumbed his own suspenders to his sides, and started unbuttoning his blue shirt while keeping his eyes locked on Dean. Dean couldn’t believe there was a man stripping a foot away while he watched Dean suck another guy’s dick, but this thought was quickly replaced by how incredibly hot it was to realize Jack was so turned on by them, to realize that Jack didn’t need them to pay attention to him, and that he was thoroughly enjoying himself just watching them finally give in to each other.

Jack cast off his button-up, and peeled off his white t-shirt in one fluid movement. He leaned down to run a thumb along Dean’s jaw before grabbing something from his overcoat, and returning to stand behind Cas. “Just try to relax, ok Cas?” Jack’s voice was ragged, his breath short with lust, and Dean recognized the click of a bottle of lube. The moment he touched Cas there Dean felt him buck forward towards his mouth. He resisted the urge to devour Cas completely and pulled off for a second.

“It’s ok Cas. It feels weird, but it’s necessary, ok?” Dean could barely see Cas’ eyes through half-closed lids, but Castiel nodded, and Dean glared at Jack as if to warn him to be gentle, to be careful. Jack nodded, clearly understanding, before Dean returned his attention to Cas’ cock, plunging it in as deep as he could to make up for the brief respite. Jack had obviously started working Cas open, because Dean could feel the poor angel actually shaking. Part of him was worried they might be overdoing it, but the other part of him wanted to see how wrecked they could get Castiel, how incredible they could make him feel. He decided to both back off slightly and level the playing field simultaneously.

He kept Castiel in his mouth, gently sliding up and down, being sure to trail his tongue along the length, and kept gently juggling Cas’ balls, but with his right hand he reached behind, and found Jack’s zipper. Jack instantly ran a hand through Dean’s hair in appreciation, and then worked with him to liberate himself. And then Dean Winchester found himself with one cock in his mouth and one in his hand, and he didn’t care because it was amazing and he was drunk as much on the whiskey as on the noises he was causing. It was the greatest power-high he had ever experienced, and he was loving every second. But he wanted more.

“Ok Castiel,” Jack’s words were rougher now, revealing his increasing arousal, “I’m going to add,” he cut off, gasped, distracted momentarily as Dean licked a stripe up the underside of his cock. He looked down in surprise to see Dean’s devilish grin looking back up at him. He had clearly had an effect, but Jack gathered himself back together. “Going to add another finger, ok?” Cas just leaned backwards, resting his shoulders on Jack’s collarbone, telling him silently to do whatever he wanted.

Dean kept rubbing Cas, slowly tugging on him and swiping his thumb over the tip, tickling underneath, while his knuckles occasionally grazed Jack’s as the more experienced man worked Castiel open. Dean returned to Jack’s cock, kissing it, refusing to take it in, but teasing the tip, licking up and down, and sliding his fingers in a tight circle up and down, along the thick shaft slick from his saliva. He relished every gasp and moan he elicited from this remarkable man who had somehow picked them up at the bar without either of them noticing. When he felt Cas buckling against Jack, he looked up, concerned, and Jack took a very large gulp before looking back at Dean.

“Maybe it’s time we move this to the bed.” The three of them moved like a single entity, all hands and mouths and moans and gasps until they collapsed on the bed in a pile of limbs and lips and fingers.

“Cas,” Jack barely got out, and Dean noticed he had started using the contracted form. For a second he was jealous, but then he realized Jack had just had his fingers inside Castiel, so it didn’t really seem very well-founded. “Cas, I need you to work Dean, like I just worked you. You need to get him ready.” And he passed him the small bottle of lube.

Castiel looked like he was ready to burst, but also seemed somewhat grateful for the respite. He was ready to lavish some of this attention back on them, now that he knew what it could feel like. Dean leaned back on the bed, and nodded to Cas, encouraging him. He also reached for Jack, brought him close so he knelt beside him, and Dean started working him as before, teasing him with his lips but mostly working him in hand. But when Cas first touched him there with a cool, slicked finger he froze, completely overwhelmed.

“Dean, are you alright? I just, I believed…” Cas looked so worried that he had done something wrong, Dean was just shaking his head.

“Nah, Cas, I’m good. I’m really, really good. I just, I’ve never been touched there. It’s new for me, is all.” And he stared deep into Castiel’s eyes, trying to tell him that he was so excited to share something with him that no one had ever had, and he thought from the half smile that crept across the angel’s face that maybe he had understood. And then when Cas grinned diabolically and returned to his task Dean was sure of it.

Castiel’s first touches were experimental and cautious. He circled a finger around Dean’s entrance with almost teasing softness. Once the initial panic subsided and Dean got over the shock of being touched in that way, it was an amazing feeling. Castiel was learning quickly. After the tenuous first touches he was enthusiastic, probing at Dean with the tip of his index finger. Dean found it difficult to split his focus between the unfamiliar sensations Cas was subjecting him to and the things he was trying to do to Jack. He decided the best course of action was to just focus on Jack.

Dean wrapped his lips around the head of Jack’s cock, flinching slightly as Castiel pressed a second finger inside him. The stretch was painful but tinged with pleasure and he felt himself relaxing around the angel’s touch. Jack hummed low in his throat as Dean lapped at his cock. He felt Jack’s hand come to rest on his head and he let Jack guide him forward, taking more of Jack’s cock into his mouth as he wrapped his hand around the base. He was worried at first that he wasn’t very good at it. It was different with Cas; Cas was inexperienced, he wouldn’t know any different. But there was no way this was Jack’s first blowjob. Was it awkward? Did Dean suck at sucking dick?

He chanced a look upwards and the look on Jack’s face proved his worries were unfounded. He watched Dean with pure delight on his face and when he noticed Dean watching him back, he licked his lips and gave him a stare that was pure sin. Dean liked that. He’d always prided himself on his ability to bring his partners pleasure. Those partners had always been women before, but the conceit was still there. Dean Winchester was good in bed, regardless of whoever else was in that bed with him, and he wanted to be good in this bed too. So he slipped his hand back to caress Jack’s balls and swallowed Jack down as deep as he dared.

Dean let out a strangled moan around Jack’s dick as Castiel pushed a third finger in and wrapped his free hand around Dean’s cock. His grip was loose like he wasn’t entirely sure what he was supposed to do with it. But just like he had been with all the other new experiences this evening, Cas was a quick learner. Dean was nothing if not responsive, and even with a cock in his mouth he found ways to let Cas know what he liked. His hips jerked upwards when Cas squeezed him just right and he groaned low in his throat when Cas flicked his thumb across the slick head of Dean’s cock, and when Cas’ fingers chanced to brush across Dean’s prostate, his entire body responded. Jack laughed softly at that, stroking his fingers through Dean’s hair gently and taking in the mischievous smile on Cas’ face.

“What is it that you find humorous, Jack?” Castiel asked. He didn’t let up on Dean as he spoke.

“I was just thinking, if that’s what you can do to Dean with your hands, imagine how he’d respond to your mouth.” Dean didn’t try to stop the groan that escaped his throat at the mental image conjured up by Jack’s words. “I think he likes that idea, Cas,” Jack crooned almost conspiratorially. He let out a pleasant sigh as Dean’s hand and mouth continued to work his hard cock. Dean wondered if it was possible to pass out from sheer pleasure. He had a feeling he was about to find out.

He was expecting Cas to be hesitant with that suggestion, but he needn’t have worried. Castiel took to his cock like a fish to water. The wet heat of his mouth enveloped Dean’s aching dick almost as soon as Jack teased at the idea, fingers still dragging in and out at a leisurely pace. Jack’s suspicions were well-founded. It’s not that Dean was easy, he tried to tell himself. It’s not that it had been forever since someone had their mouth on his dick, licking and sucking and teasing him with lips and tongue. It’s just that Castiel’s mouth was amazing. The angel had given literally zero head in his life, had probably never even considered putting a cock in his mouth before today, and he was a fucking master. It’s like he could see inside Dean’s mind, could read his thoughts and knew exactly what he wanted, what he needed. Cas didn’t waste any time teasing. He took Dean’s entire length into his mouth at once, making obscene sounds with his lips as he slid back up to suck at the tip. Dean could barely control himself, or maybe he didn’t want to. His own lips slid off of Jack’s dick to moan appreciatively at Cas’ efforts.

“Jesus Christ Cas, where did you learn to do that?!” Dean groaned as Cas licked at his cock hungrily. His head was swimming now and his breath came in ragged gasps. He wondered how long he could last like this. Cas was going to be the death of him.

“Not from the Pizza Man, if that’s what you’re wondering,” Cas dragged his lips off of Dean for just a moment to murmur a reply. Dean snorted a laugh in reply, but it quickly turned into a whimper as Cas mouthed at his balls. Jack stepped away from the bed and Dean let his hand slip off of the man’s raging erection. As he moved, he dragged a hand down Dean’s body, letting his fingers graze over the muscles of his chest, the bones of his ribs, the flesh of his belly. He smoothed his palm over the muscles of Castiel’s back, then slipped his hand between Cas’ legs and stroked his neglected cock as he settled on his knees behind the angel.

Cas’ breath was hot on Dean’s skin as he kissed his inner thighs. It was sweet, almost tender; in start contrast to the lurid and somewhat depraved nature of everything else they were undertaking. He couldn’t be bothered to get worked up about it though. He was too worked up about the sex.

“I think that’s enough foreplay, don’t you, boys?” Jack offered like it was a casual suggestion, but the low tambour of his voice, the roughness placed there by lust and desire, made it clear where his opinion stood. His hips urged Castiel forward as he spoke. Cas pulled his lips away from Dean, his breathing shallow and ragged. He lifted himself up and moved forward to bring his body closer to Dean’s. His hands were strong but gentle as he lifted Dean’s legs up to either side of his hips and then he paused. Dean thought the anticipation might kill him.

Jack held Cas’ hips and guided them forward, thumbs sliding over their heavenly definition as he helped him line up with Dean’s most sensitive spot. By this point Dean was a wrecked mess, and his breathing was ragged and hungry. He looked deeply into Cas’ eyes, and saw him piercing into his. Dean felt completely exposed under Cas’ penetrating gaze, naked beneath him and knowing it was about to finally happen.

“Cas, are you sure you want to do this?” With an enormous sigh he forced himself to reach forward and touch his waist on either side, hands resting just above Jack’s thumbs, pushing back slightly to pause the man’s advances. “Cas if you want to change your mind, it’s still –” His offer was cut off from the insistent lips on his own, and he could have sworn he heard Jack gasp in the distance, though he didn’t really register the other man right now.

Slowly, Cas pulled away from Dean’s mouth, eliciting a slight whimper at the sudden emptiness. “Dean, shut up. I have wanted this for years, since I first gripped you tight. I just had no idea it was….this, that would, that was…That I needed to grip you tight again.” And inches from his Dean’s face, eyes locked, Cas slid into Dean achingly slowly. They both gasped from the sudden flood of foreign sensations, and it occurred to Dean that in a sense, it wasn’t just Cas’ first time, since he had never let someone in before. It was a strangely comforting realization, and carried with it an intimacy at odds with the rough play of earlier.

“Easy boys, take it nice and slow. It’s you first time and we’ve got all night.” Jack offered the advice kindly, but there was an edge to it, almost like a command. Once more Jack had read Dean’s thoughts, also realized the newness, the fact that neither of them had ever been with a man before, that they weren’t entirely sure of the mechanics. Then again, the first time Dean had been with a girl he hadn’t really been entirely sure what he was doing, not that he would ever have admitted it, and he remembering that, decided to just relax into it, let it progress naturally, and –

“Oh _Jesus_ Cas!” The want his mouth had felt only just before was most certainly replaced by the fullness he now felt from Cas. The man had just shifted back ever so slightly but the fireworks it set off deep inside Dean had taken him by surprise, and he wanted it again, wanted Cas again, wanted this forever. He thrust his hips up to chase Cas’, and a deep, guttural moan escaped his mouth when Cas shoved in again, slowly, but with a deliberate, focused strength that was so perfectly _Castiel_. Growing more and more desperate Dean rutted up against Cas again, and he thought he might come right then when he heard the angel moan, a deep grumble that was rough and sweet and tender and hot and Dean was done with slow and easy; he wanted Castiel to fuck him, hard, now.

His hands flew up and started grasping any part of Cas he could find. They ran over his hips, his chest. He snaked a hand through that constantly mussed hair and arched back when Cas hit his sweet spot, making sunbursts explode in his eyes. God, he thought, at this rate he’d barely last. When his other hand slid to Cas’ hips his fingers grazed over Jack’s, and he thought to look behind Cas, beyond him, for the first time since Cas had entered him. Jack’s delicate features were absolutely lurid, and Dean realized he was watching the two of them while stroking himself, like it was his own personal live porno. For a second he felt that guilt of neglecting Jack again, but when he heard the stranger gasp in pleasure he remembered that Jack took what he wanted and must be enjoying this just fine. The sound of skin on skin as he fisted his own cock revealed as much.

After a little longer, amid shaky cries and tender kisses, Jack slid his hand down Cas’ back and over his ass. He gently reached forward slicked fingers to make sure Cas was still ready, and then he crawled forward, kissing Castiel’s shoulder and neck, earning gentle sighs from the angel. “Cas, may I?” Jack gently nibbled on Castiel’s shoulder, and ran his left hand idly down the man’s arm. Castiel couldn’t form words, just nodded frantically, and slowed his pace with Dean, apologizing silently for the temporary cessation. Dean just beamed up at him, suddenly burning with the thought that he was about to see Castiel be filled. Dean heard the rustle of plastic as Jack fumbled with a condom, then slid closer and slowly pushed into Castiel.

“Oh, ooooh” He managed to moan before collapsing onto Dean, resting his forehead on the man’s collarbone as he trembled from the added sensation. Jack sighed as he bottomed out inside Castiel’s ass, and gently ran his hands down the man’s back while smiling at Dean, letting them all adjust to this addition to their activities. Then winking a look of pure sex at Dean, Jack began thrusting into Castiel.

The whimpers that started to fall from the angel’s lips were filthy and sweet and Dean couldn’t decide whether Cas looked more adorable or tantalizing. But then he himself was gasping as he felt the pressure behind Cas slide him deeper into Dean, and somewhere in the back of his mind Dean felt like Jack was going to fuck him by fucking Cas. But he couldn’t be bothered to care how foreign a concept this was, how much it should have put him on edge, because just then he felt Cas graze his prostate again, and he bucked up into it, garnering another deep moan from his angel, and Dean decided to fully cede. He sighed, and just gave himself over to it all, losing himself in the sounds and the hands and the heat of the moment.

Cas’ forehead rested on Dean’s shoulder, the sweet sound of his moaning and the heat of his breath spiking Dean’s own arousal as Jack moved the three of them in unison. He realized he’d let his hands fall limply to the mattress, and that would never do, because here was Castiel laid out on top of him, and why the hell was he not touching every part of him? He traced his hands lightly up Castiel’s arms, feeling them tremble as his fingers danced over sweat slick biceps and tight shoulders. He cupped one hand on the side of Cas’ face. Fully aware of how odd such a tender gesture was in this situation, he stroked a thumb across Cas’ jaw, drawing his focus back. Cas lifted his head off of Dean’s collarbone. His eyelashes fluttered as their eyes met. Cas was fucking _wrecked_ , Dean realized.

“You with me, Cas?” he asked, trying to be soothing. Castiel’s eyes fixed on his for a heartbeat longer and then he _growled_ , surging forward and claiming Dean’s lips in a bruising kiss. All the air went out of his lungs as Cas’ tongue invaded his mouth. Castiel’s hips shifted and he hit that spot again and every fiber in Dean’s body responded. His back arched and his fingers bit in to Cas’ arm. He cried out, but most of the sound was swallowed up by Cas, still kissing him like his life depended on it.

“Do you have any idea,” Jack’s breathy voice interrupted, “how hot the two of you are?” Dean would have blushed, if he had any shame left, if his face wasn’t already flushed and red and hot. Cas just dragged his mouth away from Dean’s and directed his ferocity at Dean’s throat. His teeth bared just slightly as he mouthed at the hot skin of his neck, nipping at the tender flesh and soothing it with wet kisses. Dean threw his head back in to the pillows as much as he could, baring all of his throat, inviting Castiel to kiss and to touch however and wherever he wanted.

Arching his back like that, he realized, shifted his hips against Cas’ and put friction on his achingly hard dick that he hadn’t even been aware was lacking. Dean groaned with pleasure as he felt the slip of his cock against Cas’ stomach and his own. He chased the friction with a slow, circular grind of his hips. It was bliss after all these long minutes of neglect, but it wasn’t enough.

Dean slid his hands down Castiel’s body. So much heat rose off the muscles beneath his fingers. His thumbs pressed bruises into Cas’ hips where he bucked up against Dean’s thighs, and he was distantly aware he’d likely have bruises of his own in the morning. The man’s hip bones were like knives and each thrust from Jack pushed Castiel into Dean with brutal force. He drank in the hot drag of skin on skin, the sensation of Cas filling him up completely. It was amazing, so incredibly hot, but he wanted, he needed. More.

Dean’s hand snaked its way between their bodies before he’d even fully formed the desire. His fingers closed around his cock with desperate need and he moaned in spite of himself. As Dean worked himself in time with the rhythm of their hips, something dark and hungry flashed across Castiel’s eyes. He kissed Dean again with a ferocity that matched the look in his deep blue eyes, then grabbed Dean’s free hand and used the strength of their combined arms to push himself upright. Jack’s hands smoothed their way around to clutch Castiel to his chest.

With their new positioning, Dean could now feast his eyes on the glorious sight that was Castiel being passionately fucked. He could see the delicious full-body blush that reddened the angel’s flesh, admire the way his muscles moved beneath his skin as his hips moved in tandem with Jack’s. And he could see Jack, his mouth hungry on any part of Castiel he could reach. Dean felt a stab of jealousy that was only slightly masked by the lust he felt at watching Cas give himself over to the pleasure of touch. Even as his lips dragged along Cas’ neck, Jack reached down and hitched Dean’s knees up, pulling him tighter against Cas, drawing deep throaty moans from Cas and Dean alike.

Now that Cas didn’t need his hands to hold himself up, he was free to use them for other purposes, and he exercised this freedom greedily. One hand flew up to grasp the back of Jack’s neck, imploring him to keep his lips, his tongue exploring Cas’ skin. The other slipped down to bat Dean’s hand away and wrap firmly around the hard length of his aching erection. His fingers moved in slippery strokes, twisting and teasing until Dean thought he might actually die from the sheer pleasure of it. Cas thrust into that sweet spot deep inside Dean just as his thumb dragged across the wet head of his cock, and Dean cried out, vision blurring and toes curling in the throes of one of the most intense orgasms he could ever remember experiencing. Every muscle in his body tensed, come spurting out in white streaks across his own belly and Cas’.

He squeezed his eyes shut as it washed over him, wave after wave of ecstatic pleasure. Because of this he didn’t see the way Castiel’s eyes grew even wider at the sight. Didn’t see the hunger that consumed his features, didn’t see his body become seized with a level of want previous incomprehensible to the angel. But he heard the sharp intake of breath, felt the hands drop to his hips and hold him in a grip Dean had previously only felt on his soul. And he felt _Castiel_. Felt his enthusiasm reach a feverish peak, felt him steal the pace from Jack, felt him devour Dean. He heard Jack moan from deep in his throat and mutter unintelligible sounds of bliss. Exhausted and still trembling from his recent release, Dean just laid there, hands weakly clutching Cas wrists where they clung to him with bruising force. Completely consumed, Cas fucked his brains out, hitting his prostate over and over again while moaning, his breath shortening, and Dean thought he might actually pass out from it all.

That’s when he felt Cas’ rhythm falter. He looked up to see Cas gasping for breath, a mild look of confusion on his face, and for a second Dean thought he might come again watching this man, this being, finally break. “It’s ok Cas, it’s what I just did. Just relax, let it –” Cas came howling out Dean’s name, voice thick with lust and pleasure and thundering over Dean’s ears just as he felt himself filled. He gasped from the foreign sensation, but continued to hold Cas’ wrists as he rode it through, stuttering into Dean a few more times before collapsing onto his chest. Dean ran tingling fingers through the disheveled black hair, sweat making it stick up at crazy angles. Cas lay there, clutching to Dean, as if he were afraid he might fall off if he let go. Dean whispered soothing words to him, one hand in his hair, the other running along his back, trying to ease him through this. “You were incredible Cas.” He breathed out, before placing a tender kiss on the glistening forehead resting on his chest.

“Do you,” Jack’s breath was short, and he clearly was getting close himself. Dean couldn’t believe the chain reaction he seemed to have caused. With a grunt Jack tried to continue. “Two, oooh, have any idea,” he clearly didn’t have enough air to breathe and to speak, but he was just as clearly a stubborn man. Dean suspected he might just be repeating himself from earlier, and didn’t understand why he needed to finish saying it again. “How fucking hot.” But then he groaned again and gave up, one hand stroked down Castiel’s back, causing him to arch slightly, while the other hand rested on his hip. When he had arched he looked at Dean with something in his eyes, at first it looked like confusion, but then his eyes darkened again and he bit his lip. He stared at Dean with a knowing look.

“Cas, are you? You’re not seriously…?” His question was answered by the ferocious kiss with which Cas plied his lips, while simultaneously he propped himself up again, hands on either side of Dean’s chest, and thrust backwards against Jack, who gasped in surprise.

“Are you kidding me?” He asked with a bit of a chuckle, gazing past Cas to Dean with a look of confusion and mischief, the look of a greedy child who just learned they got to have seconds. “Jesus, you two will be the death of me.” And then Jack stopped trying to talk. Instead he wrapped an arm under Castiel’s waist, so that he could pound into him furiously while Cas continued to devour Dean’s lips, slide his tongue along the stubble of his chin, nip his throat and then work circles on the bites with the tip of his tongue. All this time Dean could feel Cas’ breath hitch, feel his arms trembling against his chest where they held him up, and could see him distorting his face in pleasure. Jack looked completely undone, face flushed, lips so full and dark Dean thought it was criminal, and sweat slicking every inch of his chiseled body. He slid a hand down Cas’ spine again, and pushed on the small of his back ever so slightly.

“Mmmmmmm” Cas growled, his voice lower than Dean had ever heard.

“There.” Dean spoke the command to Jack since he was the only one not about to come, though he wasn’t positive that was too far from true. He realized with tentative hope that watching this was quickly bringing him back. Jack didn’t need Dean’s direction, but he nodded confirmation all the same, and continued to plow into the angel, making him moan and gasp and mutter incomprehensible words. It occurred to Dean they might be Enochian, he knew people often slipped into their first language during sex, and he smirked thinking that Enochian had definitely never, ever been meant to tumble mixed with obscenities out of the lips of a wrecked angel covered in sweat and come.

“Come on Cas, do it. Come again. Jesus you’re gorgeous like this. Just feel it rise, and let it happen. Come.” He said the last word forcefully, staring right into Cas’ eyes, and he did. He gasped for breath, his whole body shaking, and Dean could feel him coming, felt it deep inside, felt it from the body quivering on top of him, felt it from the hands grasping at him as if Cas was drowning. He knew he would never forget that feeling. But his attention was wrenched back as Jack threw his head back and moaned from deep in his belly, almost as if he was pulling the sound up from the source of its’ pleasure.

“Oh! Oh! Oooohh!” And then Jack came, hands sliding down Castiel’s sweat-slick back over and over again, his hips shuddering into him still slightly, wrenching the last of his orgasm out, bucking against the spent man still trembling in Dean’s arms. When he finally caught his breath he tipped his head back down to look at his partners, and exclaimed with a proud smirk, “Well I’ll be damned.”

He slowly slipped out of Castiel, but when Castiel moved to do the same Dean found himself gripping him tighter, holding him in place. Jack just put a gentle hand firmly on the small of his back, and though looking at Dean, he whispered to Cas, “Stay.” He collapsed on the bed beside them, panting slightly, and tugged off the condom, tying a knot in it and tossing it on the end table. Then he rolled over to face them, propping his head up on one hand and tracing whichever parts of their bodies he could easily reach with a slow and tender fingertip. “You two were amazing. I can’t believe how in sync you were.” He chuckled again slightly, and Dean was startled to realize it didn’t bother him as much anymore. “I can’t believe…You both really didn’t know?” He shook his head incredulously, looking from the eyes of one to the other. Dean looked down at the precious creature still on top of him, still in him, and doesn’t know how they didn’t figure this out before. Cas managed to raise his head slightly and looked deep into Dean’s eyes, piercing through him like he always did, and Dean knew suddenly that it had always been there, they just hadn’t known what it was.

“We know now.” Was all he said, still gently carding a hand through the exhausted man’s dark hair. Dean barely dared to imagine it could be like this, hardly let himself start imagining if this could be their new normal. Well, except for Jack. Right on cue the man leaned forward and kissed Dean on the cheek, and Cas on his still damp brow, and then pushed himself out of bed and started gathering his things. He spoke as he dressed.

“Well boys, that was incredible. Just…definitely in my top five, and trust me when I say that’s more than a lifetime worth of competition there.” He shrugged off Dean’s quizzical expression, sliding his suspenders back into place, and Dean still couldn’t really remember how they got from Jack taunting them in his suspenders to Jack fucking them without them. But it didn’t really matter, he thought, squeezing Castiel closer.

The gesture seemed to spur Cas into action, and he looked up to the man leaving their lives forever. “Thank you Jack. It was truly a pleasure.”

He was greeted with a full belly laugh as Jack shook his head and answered, “That’s apparent. But, trust me, the pleasure was mine.” He smiled at them and made a gesture almost like a bow before adding “Gentlemen,” winking, and walking out the door.

The room felt immensely empty and quiet all of a sudden, and Dean was struck with the incredibly new sensation that he and Cas were naked in bed together. Cas finally shifted and slid out, and Dean gasped both at the empty feeling and the awareness of how hard he had become. As they lay on their sides, legs intertwined and fingers idly tracing each other’s skin, Dean took a deep breath, gulped nervously, then looked at Cas with his most devilish grin.

“What do you say, Cas, ready for round two?”

**Author's Note:**

> This was written in a round-robin format, with some editing sessions thrown in to make sure the voice stayed consistent as the work was passed back and forth. The Track Changes function on Word is glorious, both for its ability to show what has been changed, and also because then we can write things in the margins like “You are the biggest fan girl, I swear. I can’t believe you used an actual line of Jensen’s from when he meets people in person,” “did you seriously just write heat of the moment?” “What? You’re the one who wrote The Sex!”. And yes we totally gave Dean a Mal line, sue us. Love you crazy weirdoes!


End file.
